Originally Posted by Blackhood
OP this is the model that I find to be most useful (In the sense that people can actually use it, and isn't just a crazy hypothetical)
Assume the suit costs $1,000 to make your percentages easier.
Suit - 1,000
Shoes - 250 - 350 (Very long term investment, up to 10 years)
Shirts - 85 - 125
Tie - 85 - 125 (Another long term purchase, wear them for 5 years or more)
Handkerchiefs - 25 - 75 (Another long term one, there is no reason that you shouldn't be buried in your first pocket handkerchief.)
It is also worth considering that to a "layman" if you are wearing a $1000 suit, you can get away with a polyester tie and basic shirt because of a "halo" effect. True clothing nerds will notice but they make up a very small section of the populace. Cheap shoes on the other hand, always look like cheap shoes.
I agree with the above as a reasonable framework. I don't agree with ever resorting to polyester ties, particularly with a $1k suit. Decent quality silk ties can be had for a good deal less than the sum designated above, and would be preferable to polyester in almost every case. Heck, exceptional ties are available pretty much every day here on SF in the $40-60 range.
A few other random thoughts for the OP:
1) Among gents who are otherwise well put-together, shoe seem to be the most consistently undervalued element. I have seen very nice suit / shirt / tie ensembles paired with shoes that would have looked like cheap crap when brand new, but after several wearing with zero polishing, look like they belong in the garbage. Please don't drop the ball here. Get decent quality shoes and take care of them.
2) Watches are their own thing. If you get into them in any kind of significant way, your perception of value relative to the rest of your wardrobe will be permanently and significantly skewed. If you are remotely inclined along that path, my recommendation would be to flee while you can. Just get something simple and inexpensive that doesn't look jarringly wrong with a suit. Avoiding the gigantic wrist-clocks that dominate the horological landscape at present would be a good start.